As the 1960s went on, police harassment worsened along with the deepening crisis in Vietnam: Because San Francisco was a major military deployment center, city officials encouraged vice crackdowns (supposedly as an effort to keep troops ready to fight), particularly for gay bars which catered to closeted military men. Transgender women were frequently arrested on “suspicion of prostitution” when going about their daily lives—their only suspicious behavior being their gender presentation. As Stryker explains in her book, “They might be driven around in squad cars for hours, forced to perform oral sex, strip-searched, or, after arriving at the jail, humiliated in front of other prisoners. Transgender women in jail often would have their heads forcibly shaved, or if they resisted, be placed in solitary confinement in ‘the hole.’”
Elizondo remembers bars with signage warning patrons to enter at their own risk because of the regular police raids. “The cops could arrest you for anything, like for standing too long on the sidewalk, or walking down the street,” Elizondo says. “When they hadn’t met their quota of arrests, they’d come to the Tenderloin and lock us up.”
Official disdain for trans residents also meant that crimes against them were rarely investigated. “A lot of girls got killed and robbed. I think one of the girls got thrown off a second-story floor,” Elizondo continues. “You see, the trouble was, people would come to the Tenderloin to start a new life, but we didn’t know where they’d come from or their real names or anything. It was like opening a door and going through to the other side, becoming a brand new person. I was Bob; I was Diane; I was all kinds of names.”
By the summer of 1966, relations between the disenfranchised queer residents and San Francisco officials were strained, to say the least. In July, a group of LGBTQ youth in the Tenderloin founded Vanguard, which organized public demonstrations and published a self-titled magazine promoting tolerance and social justice. Vanguard held many of its meetings at Compton’s Cafeteria and its members recognized the increasingly discriminatory behavior of the restaurant’s management towards its gender-nonconforming customers. On July 18, working in partnership with other homophile groups, Vanguard staged a picket line protest at Compton’s, though the restaurant remained unsympathetic to their pleas.